Sodium Sulfite → HCID 86591385, compound

HRID 1794462Notes

Reaction equation

HRID 1794462 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:33])[CH2:18][CH2:19][C:20]2[CH:21]=[N:22][O:23][C:24]=2[C:25]2[CH:30]=[CH:29][C:28]([S:31][CH3:32])=[CH:27][CH:26]=2)=[CH:12][CH:11]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].ClC1C=CC=C(C(OO)=[O:42])C=1.S([O-])([O-])=O.[Na+].[Na+]>O1CCCC1>[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:11]=[CH:12][C:13]([NH:16][C:17](=[O:33])[CH2:18][CH2:19][C:20]2[CH:21]=[N:22][O:23][C:24]=2[C:25]2[CH:30]=[CH:29][C:28]([S:31]([CH3:32])=[O:42])=[CH:27][CH:26]=2)=[CH:14][CH:15]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 87889728HCID 87889728, compound

Product 1

HCID 86591385HCID 86591385, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N-[4-(diethylphosphonomethyl)phenyl]-3-[5-(4-methylthiophenyl)-4-isoxazolyl]propionamide (98 mg), m-chloroperbenzoic acid (60 mg) and tetrahydrofuran (5 ml) was stirred at room temperature for 4 hr. 10% aqueous sodium sulfite solution was added to the reaction mixture and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with 10% aqueous potassium carbonate solution, and then with saturated brine, dried (MgSO4) and concentrated. The residue was purified by preparative HPLC to give N-[4-(diethylphosphonomethyl)phenyl]-3-[5-(4-methylsulfinylphenyl)-4-isoxazolyl]propionamide.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with 10% aqueous potassium carbonate solution
  3. dry with materialwith saturated brine, dried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-5bac7b5f39e54cfb9d20be763179fb22
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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